IDNNA

IDNNA
Clinical data
Other names4-Iodo-2,5-dimethoxy-N,N-dimethylamphetamine; 2,5-Dimethoxy-4-iodo-N,N-dimethylamphetamine; N,N-Dimethyl-DOI
Routes of
administration		Oral[1]
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-(4-iodo-2,5-dimethoxyphenyl)-N,N-dimethylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H20INO2
Molar mass349.212 g·mol−1
3D model (JSmol)
  • Ic1cc(OC)c(cc1OC)CC(N(C)C)C
  • InChI=1S/C13H20INO2/c1-9(15(2)3)6-10-7-13(17-5)11(14)8-12(10)16-4/h7-9H,6H2,1-5H3 Y
  • Key:XBCUSBRGRALQID-UHFFFAOYSA-N Y
  (verify)

IDNNA, also known as 4-iodo-2,5-dimethoxy-N,N-dimethylamphetamine or as N,N-dimethyl-DOI, is a chemical compound of the phenethylamine, amphetamine, and DOx families.[1][2][3] It is the N,N-dimethyl derivative of the psychedelic drug DOI.[1][2][3]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists IDNNA's dose as greater than 2.6 mg orally and its duration as unknown.[1][2][3] IDNNA produced no effects at tested doses.[1] Higher doses were not assessed.[1]

Chemistry

Synthesis

The chemical synthesis of IDNNA has been described.[1]

Analogues

Analogues of IDNNA include DOI, N-methyl-DOI, methyl-DOB (N-methyl-DOB), Beatrice (N-methyl-DOM), N-methyl-DOET, N-methyl-2C-I, and N-methyl-2C-B, among others.[1][2][3]

History

IDNNA was first described in the scientific literature by Alexander Shulgin and colleagues in 1982.[4] Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1]

Society and culture

Canada

IDNNA is a controlled substance in Canada under phenethylamine blanket-ban language.[5]

United Kingdom

This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.[6]

See also

References

  1. ^ a b c d e f g h i j Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. IDNNA Entry
  2. ^ a b c d Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. The N,N-dimethyl homologue of DOI was called IDNNA (2,5-dimethoxy-N,N-dimethyl-4-iodoamphetamine) and, although not active at levels where DOI would be, it led to an extensive series of some 15 mono- and di-N-alkylated amines related to DOI. They were prepared for studies of 131I labelled compounds for rat pharmacology (and eventual 122I PET scanning agents for human studies) but none of them had been clinically explored.
  3. ^ a b c d Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 13 November 2025. Retrieved 23 February 2026.{{cite book}}: CS1 maint: bot: original URL status unknown (link)
  4. ^ Sargent T, Shulgin AT, Mathis CA (1982). "New iodinated amphetamines by rapid synthesis for use as brain blood flow indicators". Journal of Labelled Compounds and Radiopharmaceuticals. 19 (11–12): 1307–1308. doi:10.1002/jlcr.2580191102. Archived from the original on 2025-07-12.
  5. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  6. ^ "UK Misuse of Drugs act 2001 Amendment summary". Isomer Design. Archived from the original on 22 October 2017. Retrieved 12 March 2014.
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